Weird History
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13 Suave Playboys From Throughout History Who Are Actually Total Scumbags

Updated September 23, 2021 6.9k votes 1.3k voters 56k views13 items

List RulesVote up the “charismatic” and “charming” historical figures who were, in fact, cheap manipulators obsessed with sexual conquest.

For centuries, society has cheered on men who rack up the greatest number of “conquests” - conquests of women, that is. In some circles, sleeping with thousands of women is ostensibly a badge of accomplishment. Even several popes have bragged about their illicit encounters. Unsurprisingly, many of the biggest playboys in history are also some of the most infamous figures. 

When Fidel Castro wasn't palling around with Che Guevara, he was scouring the beaches of Havana for his next “meal.” Pablo Picasso drove two of his lovers to end their own lives. Henry VIII executed two of his wives. But at least one of the men repented shortly before his passing, warning others not to idolize his freewheeling lifestyle.

From Lord Byron to Hugh Hefner, these lotharios were not the greatest male lovers in history - they were historical womanizers who are only now being exposed for their exploits. Weigh in on the sleaziest playboys in history.

  • Crooner Bing Crosby cheated on his wife frequently. Actress Joan Caulfield was only 22 when Crosby, then in his 40s, had an affair with her. Crosby even requested permission from the Catholic Church to divorce his wife so that he could marry Caulfield. When his request was denied, Bing ultimately stayed with his wife, although his adulterous habits continued.

    Other reports from his family corroborate that Crosby's public persona differed from his demeanor at home.

    • Age: Dec. at 74 (1903-1977)
    • Birthplace: Tacoma, Washington, United States of America
    • Nationality: United States of America
    • Profession: Entrepreneur, Singer-songwriter, Film Producer, Golfer, Actor
  • Photo: Columbia Pictures Corporation / Wikimedia Commons / Public Domain

    Frank Sinatra had a long list of lovers, and rumors linked him to Elizabeth Taylor, Natalie Wood, and Jackie Kennedy. He also slept with showgirls in massage rooms and introduced his friend John F. Kennedy to beautiful women for the latter to seduce.

    Sinatra's third wife, Mia Farrow, was five years younger than his daughter. Throughout his life, Sinatra had multiple affairs and was often seen yelling at women in public. 

    • Age: Dec. at 82 (1915-1998)
    • Birthplace: Hoboken, New Jersey, United States of America
    • Nationality: United States of America
    • Profession: Conductor, Film Producer, Actor, Singer
  • Photo: Unknown / Wikimedia Commons / Public Domain

    Lord Byron was a poet, celebrity, and playboy in the early 19th century. In the one year he spent in Venice, he accumulated 250 female lovers. Lord Byron also slept with men and traveled to Greece to seek out male partners.

    He fled from England after rumors of his numerous affairs surfaced. His partners included aristocrats, actresses, servants, and prostitutes, although he ultimately married his half-sister. In order to keep a record of his conquests, he reportedly kept clippings of hair from his lovers' privates. 

    • Age: Dec. at 36 (1788-1824)
    • Birthplace: London Borough of Harrow, London, United Kingdom
    • Nationality: England
    • Profession: Poet, Politician
  • Photo: White House Press Office / Wikimedia Commons / Public Domain

    John F. Kennedy famously had an affair with actress Marilyn Monroe - although this has never been officially confirmed - and slept with his White House secretaries, nicknamed Fiddle and Faddle.

    While JFK was lauded for his youthful good looks and extramarital affairs, they caused major political problems. The president would reportedly suffer migraines if he didn’t regularly copulate, and J. Edgar Hoover most likely used this knowledge - as well as information relating to the president's many affairs - to blackmail JFK.

    • Age: Dec. at 46 (1917-1963)
    • Birthplace: USA, Massachussetts, Brookline
    • Nationality: United States of America
    • Profession: Politician, Military Officer, Author, Writer